The anti-inflammatory agent, (S)-naproxen sodium salt has a specific rotation of +66°. The commercial preparation of the latter agent results in a mixture that has a 97% enantiomeric excess (ee). Loose H3CO Na (S)-naproxen sodium salt (a) Draw the R enantiomer of naproxen sodium salt. (b) What effect does the R enantiomer have on plane-polarized light? (c) What is the observed specific rotation of anti-inflammatory agent mixture? (d) What percentage of each enantiomer is obtained from the above commercial mixture? (e) Provide a reaction scheme for the formation of the (S)-naproxen sodium salt from "acidic" (S)-naproxen.

The anti-inflammatory agent, (S)-naproxen sodium salt has a specific rotation of +66°. The commercial preparation of the latter agent results in a mixture that has a 97% enantiomeric excess (ee). Loose H3CO Na (S)-naproxen sodium salt (a) Draw the R enantiomer of naproxen sodium salt. (b) What effect does the R enantiomer have on plane-polarized light? (c) What is the observed specific rotation of anti-inflammatory agent mixture? (d) What percentage of each enantiomer is obtained from the above commercial mixture? (e) Provide a reaction scheme for the formation of the (S)-naproxen sodium salt from "acidic" (S)-naproxen.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter3: Stereoisomerism And Chirality

Section: Chapter Questions

Problem 3.35P

See similar textbooks

Similar questions

(a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?
Simvastatin (trade name: Zocor™M) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. HOL. O CH3 H O H Ou yot H O XII H по / CH3
Diltiazem is prescribed to treat hypertension, and simvastatin is a cholesterol-lowering drug. Locate the chirality centers in each.
Consider the following compounds: CO,H СНО ОНС. ОНС CO,H H3C H. H H3C ОН ČO,H H. CH3 HỌ A B (a) Label the asymmetric carbons as R or S on each compound (A - C). (b) Which compounds, if any, are enantiomers? diastereomers? identical?
Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?
Coibacin B is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites. Assign the configuration of each chiral center in coibacin B H.
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)
Simvastatin (trade name: ZocorTM) is a pharmaceutical used to treat elevated blood lipids (i.e. high cholesterol). It contains 7 chirality centers (which allows for 128 different stereoisomers!) Determine the configuration of each chirality center. H H HO H H H H H H H H H O H H
The specific rotation of vitamin B7 in water (22°C) is +92°. A mixture of vitamin B7 and its enantiomer has a specific rotation of + 27.6°. What is the percentage of vitamin B7 and its enantiomer in this mixture? Select one: O A. 60% vitamin B7 : 40% enantiomer B. 65% vitamin B7 : 35% enantiomer C. 55% vitamin B7 : 45% enantiomer D. 70% vitamin B7 : 30% enantiomer
Determine and label the configuration of each chiral carbon in the molecule shown below. HN B O FI OH The molecule shown below is the synthetic drug Latuda (Lurasidone) that is prescribed for antipsychotic for the treatment of schizophrenia in adults and adolescents (13-17 years). Examine the molecule carefully and answer the following questions. H 'N (S) H INH (R) (S) (R) IH H (S) O (S) a) Identify and label the functional groups in the molecule. b) Confirm the configuration of each stereogenic (R/S) center the molecule. c) Label the hybridization of all the nitrogen atoms in the molecule d) Circle of the most basic atom in the molecule and estimate the pKa of the conjugate acid of the base.
How many stereogenic centers are present in the following compound? CH3CH₂CH₂CH2, H C=C H 1 02 H ||
The specific rotation of S-Ibuprofen is +54.5o. Which direction would a mixture containing 80% S-Ibuprofen and 10% R-ibuprofen rotate plane polarized light? To the left or to the right?